Ryan Caulfield

Experience

• 

  Digital River

  Dec 2007 - Nov 2024

  - Enabled successful deployment and scaling of SaaS, PaaS, and hybrid cloud solutions, ensuring high availability and performance.- Delivered strategic technical guidance to Fortune 500 clients, ensuring alignment between IT initiatives and business objectives.- Partnered with Sales and Customer Success teams to drive upsells, renewals, and expansion opportunities, contributing to a 10% increase in annual recurring revenue (ARR).- Championed the voice of the customer (VoC) internally, contributing to feature prioritization and product improvements.- Acted as a technical escalation point, resolving complex issues and coordinating with engineering, support, and product teams to ensure customer satisfaction. Show less - Identified and addressed technical blockers through proactive monitoring and support, resulting in a 20% reduction in escalations.- Created reusable solution architectures, knowledge base articles, and implementation guides, reducing support tickets and improving self-service.- Designed and executed customer success plans, delivering technical enablement, onboarding, and optimization across complex enterprise environments.- Acted as a strategic technical advisor to enterprise customers, aligning product capabilities with key business outcomes and transformation goals.- Partnered closely with Customer Success Managers (CSMs), Product, and Engineering teams to resolve technical challenges and influence product direction. Show less - Revamped internal processes to boost operational efficiency and support customer success objectives.- Mentored junior team members and supported scaling of operational frameworks, contributing to a 40% increase in team productivity.- Managed a global offshore team of 5 operations specialists, ensuring consistent service quality, workload distribution, and cross-timezone coordination.- Oversaw end-to-end client operations for enterprise accounts, ensuring seamless onboarding, issue resolution, and consistent client satisfaction.- Used data analytics to identify revenue growth opportunities, track client engagement patterns, and surface insights that drove upsell and cross-sell strategies. Show less

  • Principal Technical Account Manager

    Nov 2023 - Nov 2024

  • Principal Customer Success Engineer

    Oct 2020 - Nov 2023

  • Principal Client Operations Specialist

    Sept 2019 - Oct 2020

  • Manager, Client Operations

    Apr 2016 - Sept 2019

  • Technical Operations Manager

    Oct 2014 - Apr 2016

  • Technical Lead, Store Operations

    Jul 2012 - Oct 2014

  • Senior Store Operations Manager

    May 2011 - Jul 2012

  • Store Operations Manager

    Feb 2010 - May 2011

  • Account Coordinator

    Dec 2007 - Feb 2010